Never drafted into the league, Gerry Fleming signed as a free agent with the Canadiens on Feb. 17, 1992. He made his debut in the NHL on Mar. 24, 1994 against the Winnipeg Jets. Fleming played four other games with the Habs that same season as well as another six in the following campaign, recording no points and finishing his NHL career with 42 penalty minutes. After his career, Fleming worked as assistant coach for the Montreal Canadiens’ farm team, the Fredricton Canadiens, for the better part of the 1990s.